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Leap by Asking Better Questions

Leap by Asking Better Questions

This series is focused on making transitions in your life. For me, I’m learning this firsthand as I transition out of a career in the tech industry and explore coaching teams and emerging leaders. On one hand, the transition couldn’t have felt more obvious after years of working and growing my own teams and practices in fast moving companies. I’ve always had a coaching side hustle going on - if not in my professional world, certainly in the books I read, conferences and trainings I attend and the things I spend my time thinking about. 

However, letting go of what you know and stepping into a new life situation is a process. There are many “tips” and “tactics” that outline steps or the processes to make these changes. However, in the real So Now What scenarios, we have to ask questions that are deeper and delve into the reason and meaning behind change. As they say, “Wherever you go, there you are.”

If you aren’t asking better questions of yourself, you’ll be in different places with different faces but things won’t really change.

For me, the catalyst of my change was being asked if I was taking care of what I cared about. Of course, my first reaction was a resounding “yes!”. But as I thought more about the question, I wondered - what has meaning and depth for me? Am I taking care of the things that matter most in my life? If so, how am I taking care? If not, why aren’t I?

So, I was almost 50, I had a successful career and was doing well at a large tech company. I liked the people I worked with and I was learning quite a bit - all important things - however, my role required an amount of travel that was too much for my family. And, as my family and my health were listed as high priorities, neither were getting much attention.

And certainly, that happens sometimes - we have to double down in one aspect of our lives and other domains don’t get the focus. Things get crazy at home. Your gym membership lags for a few months. For me, the problem was that I thought I was doing pretty well in all domains and I was blind to the things i had neglected. I was blind to the full cost of my role and its impact on my life. Could I have changed how I operated in my role? Yes, of course. Could I have stayed another year or five or ten? Probably yes. 

But seeing a full picture of what I cared about and realizing I was putting resources into areas that weren’t my priority meant I was facing a decision point. Asking the questions and taking a clear-eyed look at the answers gave me more information about my life.

I decided to leave my role and give myself one year to explore, recharge and recalibrate. I recognize this is a privledged position to even have as an option, and for that I”m thankful. Without the time, I think I would have chosen to get a job that allowed me to throttle back for a bit and regroup (with a paycheck and health insurance). 

So, I’m stepping out into an unknown world. Some days the work is obvious and laid out clearly. Other days I see that there are spaces in my life I thought were defined and rigid but are actually quite flexible. Other days I see that i”m never going to be “done” its always a journey and its always a work in progress. Other days I rest. Other days I practice trust. Other days I ask for help. Other days I behave very very much in the same ways that I did in my high tech high pressure job - too busy, too stressed, missing a bigger picture or purpose in my stress.

Our society is really open about letting young people straight out of college see the world as an oyster with many choices open to them. It is more rare to hear a narrative of open choices in middle age - and certainly, different life circumstances open or close paths, but there are still many open paths. We think about them less, focusing on what we “know” or what cannot ever be changed.

unraveling some of what we were so certain about
offers a freedom and a sense of new possibilities

Questions I continue to ask myself.

  1. What do I care about? Not just in a professional domain but in my family, community, my personal life, spirituality, mental health and so on.
  2. Am I taking care of what I care about?
  3. Why do I care about these things? For the sake of what? I”m taking action for what purpose?
  4. When I talk about taking care of X or Y, how do I know I’m meeting a standard that matters to me? What’s my standard? How do I know when I”m successful?

This isn’t navel gazing, this is introspection that helps me assess whether I”m building the life I intend. Otherwise it’s easy to be very busy - but to what end? Sometimes, I have team members come to me and say they are struggling but that their team or their stakeholder is giving them great feedback. My answer is usually “Because it’s working for them! Its not working for you!”

Ask yourself, ‘Is this working for me?”. Be honest. Don’t you deserve to know and answer this question directly?


Courtney founded the Design Operations team at Facebook and spent 6 years building the discipline into an impactful team key to creating design operations excellence. Before Facebook, Courtney was Principal of Program Planning and Principal of Client Development at Hot Studio working to build a team that could scope, manage and deliver complex digital engagements. 

As a coach, Courtney partners with leaders to support them in building strong teams with clear vision and communication.

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